4-Hydroxybenzaldehyde → p-Dodecyloxybenzaldehyde

HRID 2245831Notes

Reaction equation

HRID 2245831 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH2:10](OBr)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].[OH-].[K+].CC(C)CC(O)C>>[CH2:21]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH3:10]

Participants

5

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 79104-Methyl-2-PentanolHCID 14797Potassium HydroxideHCID 86623644HCID 86623644, compound

Product 1

HCID 141069p-DodecyloxybenzaldehydeYield 77.4%

Procedure

100 g of 4-hydroxy-benzaldehyde are reacted with 224.5 g of dodecyloxybromide along with 56.7 g of anhydrous KOH (85%) in 11 of 4-methyl-2-hydroxy-pentane. The mixture is then heated to reflux and maintained at reflux for 7 hours. The cooled reaction mixture is filtered to eliminate salts and distilled in a claisen equipment. 184 g (yield 77%) of a clear oil are collected at 178-181° C. and 0.5 mbar, which slowly crystallises on standing at room temperature.

Workup

  1. temperatureThe mixture is then heated
  2. temperatureto reflux
  3. temperaturemaintained
  4. temperatureat reflux for 7 hours
  5. customThe cooled reaction mixture
  6. filtrationis filtered
  7. distillationdistilled in a claisen equipment

Sources & evidence

ORD record
ord-18b0539d161547d2b873cfe85ee5802c
Source dataset
uspto-grants-2010_03
Patent number
US07683202B2

Reaction notes

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